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Cheap flights from Montrose to Chicago from $215

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montrose to Chicago departing on 9/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Montrose to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
9:05 am - 2:20 pm
MTJ
-
MDW
4h 15m
1 stop
Southwest Logo
11:45 am - 7:35 pm
MDW
-
MTJ
8h 50m
2 stops
$320Southwest
Tue, Sep 29 - Wed, Oct 14
Southwest Logo
9:05 am - 2:20 pm
MTJ
-
MDW
4h 15m
1 stop
Southwest Logo
3:40 pm - 7:35 pm
MDW
-
MTJ
4h 55m
1 stop
$321Southwest
Tue, Sep 29 - Wed, Oct 14
Southwest Logo
9:05 am - 7:10 pm
MTJ
-
MDW
9h 05m
2 stops
Southwest Logo
11:45 am - 7:35 pm
MDW
-
MTJ
8h 50m
2 stops
$325Southwest
Tue, Sep 29 - Wed, Oct 14
Southwest Logo
9:10 am - 7:00 pm
MTJ
-
MDW
8h 50m
2 stops
Southwest Logo
2:05 pm - 6:20 pm
MDW
-
MTJ
5h 15m
1 stop
$345Southwest
Fri, Aug 21 - Sat, Aug 29
Southwest Logo
9:10 am - 4:10 pm
MTJ
-
MDW
6h 00m
1 stop
Southwest Logo
2:05 pm - 6:20 pm
MDW
-
MTJ
5h 15m
1 stop
$349Southwest
Fri, Aug 21 - Sat, Aug 29
Southwest Logo
9:10 am - 7:00 pm
MTJ
-
MDW
8h 50m
2 stops
Southwest Logo
10:15 am - 6:20 pm
MDW
-
MTJ
9h 05m
2 stops
$350Southwest
Fri, Aug 21 - Sat, Aug 29
Southwest Logo
9:10 am - 6:55 pm
MTJ
-
MDW
8h 45m
2 stops
Southwest Logo
4:35 pm - 7:50 pm
MDW
-
MTJ
4h 15m
1 stop
$371Southwest
Thu, Aug 27 - Sun, Aug 30
Southwest Logo
9:10 am - 6:55 pm
MTJ
-
MDW
8h 45m
2 stops
Southwest Logo
3:50 pm - 7:25 pm
MDW
-
MTJ
4h 35m
1 stop
$375Southwest
Thu, Sep 3 - Tue, Sep 8
Southwest Logo
9:10 am - 6:55 pm
MTJ
-
MDW
8h 45m
2 stops
Southwest Logo
1:30 pm - 7:50 pm
MDW
-
MTJ
7h 20m
2 stops
$377Southwest
Thu, Aug 27 - Sun, Aug 30
Southwest Logo
9:10 am - 4:10 pm
MTJ
-
MDW
6h 00m
1 stop
Southwest Logo
3:50 pm - 7:25 pm
MDW
-
MTJ
4h 35m
1 stop
$379Southwest
Fri, Sep 4 - Tue, Sep 8

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Southwest flights from Montrose to Chicago Midway Airport

Our best Southwest deals on Montrose to Chicago Midway Airport flight tickets
Southwest
Sep 29
MTJ9:05 amMontrose County
4h 15m
1 stop
MDW2:20 pmChicago Midway
Oct 14
MDW11:45 amChicago Midway
8h 50m
2 stops
MTJ7:35 pmMontrose County
$320
Southwest
Sep 29
MTJ9:05 amMontrose County
4h 15m
1 stop
MDW2:20 pmChicago Midway
Oct 14
MDW3:40 pmChicago Midway
4h 55m
1 stop
MTJ7:35 pmMontrose County
$321
Southwest
Sep 29
MTJ9:05 amMontrose County
9h 05m
2 stops
MDW7:10 pmChicago Midway
Oct 14
MDW11:45 amChicago Midway
8h 50m
2 stops
MTJ7:35 pmMontrose County
$325

momondo Fare Finder

 
Customize your flight search to find flights from Montrose to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 2, 2026.
Use the filters below to find and compare flights from Montrose to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Tue 9/29

9:05 am-2:20 pm

1 stop4h 15m

Chicago Midway

Wed 10/14

11:45 am-7:35 pm

2 stops8h 50m

$320
Quickest round-trip

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Tue 9/29

9:05 am-2:20 pm

1 stop4h 15m

Chicago Midway

Wed 10/14

3:40 pm-7:35 pm

1 stop4h 55m

$321

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Tue 9/29

9:05 am-7:10 pm

2 stops9h 05m

Chicago Midway

Wed 10/14

11:45 am-7:35 pm

2 stops8h 50m

$325

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 8/21

9:10 am-7:00 pm

2 stops8h 50m

Chicago Midway

Sat 8/29

2:05 pm-6:20 pm

1 stop5h 15m

$345

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 8/21

9:10 am-4:10 pm

1 stop6h 00m

Chicago Midway

Sat 8/29

2:05 pm-6:20 pm

1 stop5h 15m

$349

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 8/21

9:10 am-7:00 pm

2 stops8h 50m

Chicago Midway

Sat 8/29

10:15 am-6:20 pm

2 stops9h 05m

$350

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Thu 8/27

9:10 am-6:55 pm

2 stops8h 45m

Chicago Midway

Sun 8/30

4:35 pm-7:50 pm

1 stop4h 15m

$371

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Thu 9/3

9:10 am-6:55 pm

2 stops8h 45m

Chicago Midway

Tue 9/8

3:50 pm-7:25 pm

1 stop4h 35m

$375

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Thu 8/27

9:10 am-6:55 pm

2 stops8h 45m

Chicago Midway

Sun 8/30

1:30 pm-7:50 pm

2 stops7h 20m

$377

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 9/4

9:10 am-4:10 pm

1 stop6h 00m

Chicago Midway

Tue 9/8

3:50 pm-7:25 pm

1 stop4h 35m

$379

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Montrose to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Montrose County to Chicago Midway?

Southwest is the most popular carrier operating from Montrose County to Chicago Midway

When to book flights from Montrose to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Montrose to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Montrose to Chicago Midway Airport (MTJ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montrose to Chicago Midway Airport

Fastest flight time

4h 15m

Direct flights

None
The fastest flight from Montrose to Chicago Midway Airport takes 4h 15m
There are no direct flights from Montrose to Chicago Midway Airport. There are no popular flight routes from Montrose to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Montrose to Chicago Midway Airport

  • How far is Montrose County to Chicago Midway by plane?

    Montrose County and Chicago Midway are 1084.3 mi apart from one another. Typically, this will take 4h 15m by plane in normal conditions.

  • When did momondo last update prices for flights from Montrose County Airport to Chicago Midway Airport?

    Prices for flights from Montrose County Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Montrose County Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Montrose County Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

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Munster
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Why use momondo?

Why should I use momondo to find a flight deal from Montrose to Chicago?

Finding the right flight to Chicago from Montrose is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Montrose to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Montrose to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Montrose to Chicago?

Once all potential Montrose to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Montrose to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Montrose to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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